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Neighborhoods: Streets to walk through in Chicago

Hi All,

My girlfriend and I are in our late 20s, early 30s and considering moving to Chicago one day.

We're from NYC and of course accustomed to surroundings that are more dense given our time in the Upper East Side and Park Slope, Brooklyn. We don't plan on owning a car and enjoy walking everywhere/public transportation.

We've visited Chicago a few times and have walked around a few neighborhoods. We realize it is not as dense as NYC. From what we saw, we felt Lincoln Park or perhaps parts of Lake View or Bucktown were more of a fit but most streets we walked were a combination of a bunch of things to do and then nothing around.

We're going to head back in a month to do another similar round of walking through neighborhoods.

**Would love to know what are some of the more fun/denser streets (or stretches) to walk down to get a feel of the area we'd live in??**

(we love little coffee shops, neighborhood bars, running outside/parks, and the gym is a part of our daily lives - though that could exist near wherever we work). Anything that reminds me more of Park Slope would be great!


6 Answers

top answer by
Crystal from Anchorage


Chicago is my favorite US city (although I love New York too). I have lived there on and off since 2006 and have lived in a variety of neighborhoods. I have visited both Park Slope and the Upper East Side, so I know what you mean by density. Chicago overall is definitely not as dense as NYC, and it will be hard to find a neighborhood that is comparable in that way. 

I think you are on the right track with Lakeview, Lincoln Park, and Bucktown.

Here are a couple of other neighborhoods to walk on your next visit:

Old Town- Definitely charming and close to the Loop.

Lakeshore East- Right downtown at the north end of Millenium Park, Maggie Daley Park, and Grant Park.

South Loop- At the other end of Grant Park, this area has completely changed in the last 20 years from scary and crime ridden to brand new high rise apartments. It puts you right near the Museum Campus in an area that is quickly gaining popularity. Keep your eyes out for new restaurants, cafes, etc.

Printer's Row- Basically a micro neighborhood in the South Loop. It has the older vintage high rises with refurbished apartments.

Andersonville- It was once the home to Scandinavian immigrants, and while you can still see evidence of that it is very multicultural now. It has good nightlife, but overall has a more mature feeling.

If you do walk Lakeview again, be sure to walk along Broadway, Clark, Belmont, Halsted, Southport, and Addision. They all have their own vibes. Out of those streets I would say Southport is the most comparable to Park Slope in Brooklyn.

If in Bucktown again the streets to walk are Damen, Milwaukee, Fullertron, and North Ave. Be sure to head south to Wicker Park too along Damen and Division. Wicker Park was definitely known for it's hipsters, which are definitely still there, but has been developing into a more "mature" neighborhood.

For Lincoln Park, walk Fullerton, Clark, Halsted, Lincoln, Armitage, and Sheffield. 

Well that probably is more than enough information for now. Good luck!

Mentioned in this answer:

  1. Chicago (city)
  2. Old Town (attraction)
  3. Lakeshore East (attraction)
  4. South Loop (attraction)
  5. Printer's Row (attraction)
  6. Andersonville (neighborhood)
  7. Lakeview (attraction)
  8. Bucktown (neighborhood)
  9. Wicker Park (neighborhood)
  10. Lincoln Park (attraction)
3 thankscomments (1)

answered by
Courtney from Los Angeles

Hey, Andrew,

I'm not that familiar with Chicago but I'm very familiar with Park Slope and I'd say that the Wicker Park area has kind of the same feel, although Park Slope might be slightly more upscale. Very neighborhood-y, tons of cute restaurants, lots of little shops. Just a suggestion!

Mentioned in this answer:

  1. Wicker Park (neighborhood)
1 thankscomments (1)

answered by
John from Chicago

I would recommend you check out the Gold Coast. It's an area that has a lot of stuff within walking distance (and it's often hard to park, so that's a good indication of what you're looking for). You can live in a condo and walk around 900 N Michigan Ave which will give you a lot more crowds if you don't mind the tourists. There is stuff going on at night with bars and restaurants.

Lincoln Park, Lakeview and Bucktown are kind of their own cool neighborhoods, but they all have the main streets you walk down, and then the side streets that are residential and can be much quieter. A lot of people like this because they can live on a quiet street but walk a block over to quickly get to restaurants and shops without driving. Coming from NYC that's probably not your criteria.

Definitely avoid downtown Chicago and the loop, sometimes people think they want to live "downtown" where everything is happening, but in Chicago downtown is definitely dead at night, it's just for office buildings and people working during the day.

I don't know if South Loop is going to be busy enough for you. It's building up, but right now there are plenty of condo buildings and not a ton of shops and restaurants packed closely together yet.

Another place you might want to check out is River East, near the AMC River East 21. Same idea as Gold Coast, you can live in a nice condo with a view of the lake, then walk easily up and down Michigan Ave, State St, and over to Navy Pier.

Oh, and coming from NYC, you'll easily afford a nice place in a great location, so in general stay close to the lake since that's a huge appeal of Chicago (especially in the summer).

Mentioned in this answer:

  1. Gold Coast (neighborhood)
  2. 900 N Michigan Ave (attraction)
  3. AMC River East 21 (attraction)
1 thankscomments (2)

answered by
Melody from Chicago

No one has mentioned Pilsen. This is a vibrant neighborhood that doesn't get as much attention as say, Wicker Park or Logan Square (skip River North or Gold Coast, there are tons of tourists there.) Start at Halsted Street and 18th street and walk west toward Damen Blue Line Stationand you will get a fairly decent taste of what the neighborhood has to offer (walk back along 16th street and check out the murals.) 

Mentioned in this answer:

  1. Pilsen (attraction)
  2. Wicker Park (neighborhood)
  3. Logan Square (attraction)
  4. River North (neighborhood)
  5. Gold Coast (neighborhood)
  6. Halsted Street (attraction)
  7. Damen Blue Line Station (attraction)

answered by
Vince from Sarasota


I see you have altready received some good suggestions on areas/neighborhoods to walk around in Chicago.

It all depends where you will staying to start with and where you can afford and prefer to live in. Young people like and try to live in Lincoln Park which has gotten expensive so the more affordable areas are: Wicker ParkBucktownDePaul University area. I would recommend a reputable realtor to guide you and take you around.

As far as walking for enjoyment I would recommend walking from the Loop or Rush and State north on State toward North Avenue and to Lincoln Park Zoo  which is free. Also on the water front from Navy Pier to North Ave and beyond. Also walk around Wrigley Field Halstead and Sheffield), Old Town which consist of around North and Wells, the Museum Campus and Hyde Park around the University of Chicago campus, and Little Italy District around Taylor st. and the U. of Illinois Chicago campus. A must is to walk to Millennium Park  across the wooden bridge and go to Grant Park and the Buckingham Fountain all the way to Soldier Field and Field Museum of Natural History , and the Shedd Aquarium and John Hancock Observatory.

Go to the Chicago Cultural Center  on Randolph and Michigan and pick up maps, guides and brochures, El's schedules and all kinds of tourist's info. Also take a boat tour of the Chicago River and the lake front.

I lived in Chicago (downtown) for 30 years and walked all over every week-end and I have only seen 25% of the city it is so big and diverse as well as gorgeous. Enjoy....

Mentioned in this answer:

  1. Lincoln Park (attraction)
  2. Wicker Park (neighborhood)
  3. Bucktown (neighborhood)
  4. DePaul University (attraction)
  5. Lincoln Park Zoo (attraction)
  6. Navy Pier (attraction)
  7. Wrigley Field (attraction)
  8. Old Town (attraction)
  9. Little Italy District (neighborhood)
  10. Millennium Park (attraction)
  11. Grant Park (attraction)
  12. Buckingham Fountain (restaurant)
  13. Soldier Field (attraction)
  14. Field Museum of Natural History (attraction)
  15. Shedd Aquarium (attraction)
  16. John Hancock Observatory (attraction)
  17. Chicago Cultural Center (attraction)

answered by
Courtney from Los Angeles

Hey, Andrew,

I'm not that familiar with Chicago but I'm very familiar with Park Slope and I'd say that the Wicker Park area has kind of the same feel, although Park Slope might be slightly more upscale. Very neighborhood-y, tons of cute restaurants, lots of little shops. Just a suggestion!

Mentioned in this answer:

  1. Wicker Park (neighborhood)

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